


Dean's First Prostate Massage

by LastAng3L



Category: Supernatural
Genre: Alternate Universe - College/University, Castiel and Dean Winchester are Roommates, Castiel is a Good Friend, Dean Needs A Hug, Dean needs Sex-Ed, Drunk Dean Winchester, Dubious Consent, Dumb Blonde Dean, Dumb as rocks Dean, Engineering Student Castiel, Jock Dean, M/M, Nerd Castiel, Party Boy Dean
Language: English
Status: Completed
Published: 2017-09-03
Updated: 2017-09-03
Packaged: 2018-12-23 09:49:36
Rating: Mature
Warnings: Rape/Non-Con
Chapters: 1
Words: 2,695
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11987328
Author URL: https://archiveofourown.org/users/LastAng3L/pseuds/LastAng3L
Summary: If you ask Dean what happened last night after the game, his response will be kind of fuzzy. All he knew for sure is that he got drunk and ended up receiving a massage from his buddy Victor, who promised the most pleasurable massage he’ll ever experience. And his friend was right. He had enjoyed it.Still, for some strange reason, Dean felt confused. He had liked the massage, but he hadn’t intended to spend the night in Victor’s dorm or fall asleep in his bed.After doing what felt like "the walk of shame" to his own dorm, it  wasn’t long until his roommate and best friend, Castiel, figured out that something was off with him.





	Dean's First Prostate Massage

If you ask Dean what happened last night after the game, his response will be kind of fuzzy. All he knew for sure is that he got drunk and ended up receiving a massage from his buddy Victor, who promised the most pleasurable massage he’ll ever experience. And his friend was right. He had enjoyed it. 

After the massage was over, he was so relaxed and boneless that he fell asleep in his teammate’s bed. When he woke up the next morning, he felt a hard body next to his. It was Victor, whose chest was pressed against his back and was cuddling him in his sleep, making Dean the little spoon. 

For some strange reason, Dean felt confused. He had liked the massage, but he hadn’t intended to spend the night in Victor’s dorm. What was he, a girl? He didn’t like waking up with some dude making him his cuddle bitch. That was kinda gay... Also, the dude had a tight grip on his torso and it was a real struggle to wiggle out of Victor’s arms’ vice-like hold in order to sneak out the room without waking him up. 

He couldn’t explain why he wanted to leave Victor’s room so badly. When he did, he was almost running out of the dorm, like a bat out of hell. It was awkward waking up like that next to a guy, and it felt too much like he was doing the walk of shame. Weird. 

On the other hand, he thought he would have ammunition to make fun of his friend for eternity, or at least until he did something far more humilliating. However, he felt his stomach twist at the thought of someone finding out where, how, and with whom he spent the night. He had a feeling he’d have to take this one secret to the grave. 

But it wasn’t long until his roommate and best friend, Castiel, figured out that something happened to him. It was stupid, but he couldn’t stop thinking about what happened last night at Victor’s and when he arrived at his dorm room, Cas had immediately suspected something was wrong. Dean looked spooked, after all. 

When he didn’t respond to Cas’ nagging questions about where and with whom he’d spend the night (and the judge-y comments about his sex life and funny jabs at his expense for being the resident gigolo on campus), his friend was taken aback. Dean had no dumb –and almost pathetic– comeback or smartass insults, and was not partaking in their normal banter. So, the alarm bells went off in Cas’ huge brain.

-“Dean? What’s wrong? Why do you look like you spent the night in a haunted mansion?”, asked Castiel with as much tact as he could muster (he was tactless as hell and a borderline asshole, but at least he acknowledged it and owned it). After staring at Cas with his mouth open like a fish and no words coming out of it, he realized that he had to look like a mentally challenged person who couldn’t understand human speech. Cas was amused at first, but now he looked worried. Cas took a step toward Dean, and Dean automatically took a step back. 

-“What?”, he asked after Cas’ eyes widened and his arms came up above his head, palms open in a sign of surrender.

-“Dean, are you ok?”

-“Yeah, man. Relax.” Dean knew he was being an ass to Cas, but he didn’t care. His pride was on the line. 

-“So… Had fun last night?” Cas asked carefully, to not open the can of worms that he knew was about to explode. Like a volcano eruption, it was imminent and he knew it. 

-“…Shut up.”

-“Dean, you know I won’t judge you. You can tell me anything.”

-“Sure thing, Cassandra. Let me put on some Taylor Swift music so we can gossip about boys and discuss our feelings.”

-“If you want, Dean. Did you know there's a grain of truth in every joke?”

-“Ha ha, Cas. Are you moonlighting as a comedian, now?”

-“Can’t. I’m an engineering major. I only have time to study and breathe. Eating and sleeping are the only hobbies I can afford to have outside of my busy college schedule.”

-“Too bad, Cas. You’d kill with your patented blend of desert-dry humor and sarcasm.” Dean said this with a smirk on his face, feeling victorious after wrongfully assuming Cas would drop it and postpone their feelings talk.

-“Sure. They won’t mind that my ‘people skills’ are ‘rusty’.” After staring at each other for what seemed like forever in the living room section of their small dorm, Dean let his eyes and head drop to the tile floor. “Want some coffee, Dean?”

-“What, no tea for our little tea party?”, asked Dean, smirk and defiant look back on his face and directed at Cas.

Cas knew he shouldn’t pry, but he was genuinely worried about his best friend. He’s never seen Dean act like this. He rolled his eyes at Dean’s comment, turned around, and went to the kitchen with Dean following him so he could make his buddy some coffee. After giving him his warm cup of joe (black and filled to the brim), he saw Dean relax and exhale, releasing the long-held breath he’s been keeping inside his lungs since he walked through the front door of their dorm. 

Castiel stayed quiet and just stared at Dean with his impossibly blue, worried eyes taking in his unease and state of disarray. It was a technique Cas had learned from Sam –the bastard gave his brother's roommate his most effective psychological weapon– and was now using it to make Dean talk about his feelings. Also, Cas was like a Jedi when he wanted to be. 

Dean tried his best to stay quiet, using the coffee cup to keep his mouth busy and full. But then he couldn’t help thinking about what had happened at Victor’s, and all his confusing thoughts were going through his head a mile per second. So, he decided to budge and at least talk about it as indirectly and obtusely as he could to avoid talking about his real feelings. Damn Obi-Wan Casoby and his mind tricks!

-“Say, Cas… I have a weird ass question.” Cas kept staring at him, but now with a raised eyebrow.

-“Shoot, Dean.”

-“Let’s say that, hypothetically, a guy offers to give you a massage and you accept.” Cas, now with both of his eyebrows raised, widened his eyes, but kept quiet so Dean could continue.

-“Ok… Go on...”

-“And hypothetically, you enjoy that massage a little too much and end up falling asleep in his bed and spending the night with the guy…” Dean was being as honest and explicit as his ego and pride would allow him. Cas thought this was some kind of miracle: he was witnessing Dean show true emotional growth by talking about his repressed homosexual desires –something that, in his opinion, all men had, as all humans have the potential to be bisexual or gay.

-“…And?”, asked Cas, growing more amused by the second and waiting for Dean to let out the question he wanted to ask. 

-“And, is that gay?” If Cas had been the one drinking coffee, he would’ve done a spit-take. 

-“Is what gay?” Dean just looked exasperated at this point at Cas’ obtuseness and was starting to get annoyed. 

-“…The massage, you idiot!” Cas kept looking at him, amusement clear on his face, and put a hand over his mouth to try to hold in his laughter. But he couldn’t, and he lost it. He started laughing and was doubling over himself, about to fall on the floor. He just couldn’t control himself and be a good best friend to his slightly homophobic roommate. “CAS!”

-“…What?” The laughter wasn’t dying, and he was now on the floor assuming the fetal position. 

-“Man, you truly are an asshole.” Cas’ laughter subsided, and he now sat on the floor, back against the kitchen counter, looking at his best friend’s face, beet red from shame and anger. He decided he was going to address Dean’s question seriously, no matter how funny and absurd it was. So, he did what any best friend would do in a situation like this. He was going to listen.

Cas padded the empty space next to him on the floor, asking Dean to sit down with him. To his surprise, Dean did. They were quiet for a good 30 seconds, until Cas resumed the conversation.

-“No, Dean. I don’t think enjoying a massage from a guy, as a guy, is gay. And I don’t think spending the night with a guy, as a guy, is gay.”

-“…But what if you wake up in a guy’s bed, naked, and being cuddled by the guy who gave you the massage?”

-“Hmm… I’d need more details in order to produce an opinion that’s more informed.” It was Dean’s turn to laugh at Cas now. The guy was like a robot sometimes.

-“Ok… I’ll try to give you more –hypothetical– details…” Cas smiled wide at his best friend, mirth and amusement –and affection– in his eyes, and a silent plea of ‘Please, continue.’ Dean significantly relaxed more. “Say, hypothetically, that I went to Victor’s after the game… After getting very, very drunk at a party last night…”

-“Uh-huh... And?”

-“And the guy offered to give me a massage so I could ‘relax’ my muscles, which were hurting from straining them on the field during the game.” Cas had taken a massage course once, so he was curious about Victor’s technique.

-“So, what kind of massage did Victor give you?” Dean glared at him for a moment and Cas frowned. Then, he realized he had forgotten to add the magic safe word to his question. “Hypothetically…”

-“He gave me a full-body massage… A ‘sports’ massage, or so he said. Then, when he realized that my penis had perked up from his ministrations and was at half-mast, he offered to give me a… prostate massage… He said it wasn’t the same thing as a ‘happy ending’, but that it had the same effect.” Castiel just stared mouth agape at Dean, trying to understand what his friend was saying.

-“…A ‘prostate massage’?” Cas had never heard of any masseuse or masseur using that massage technique –professionally, at least. Dean’s face got two shades of red darker. Cas knew he’d have to thread carefully from now on or Dean would close up and stop talking. So, he waited for Dean’s answer. 

-“…Yes.”

-“So, hypothetically… How did it feel?” Dean took a deep breath and decided to tell Cas more about his experience last night with Victor. If somebody was going to be understanding AF, it was going to be Cas.

-“It felt… Good. Too good…” Dean sighed, took another deep breath, and continued. “He started with his fingers first, using lube, and said that my prostate was easy to find. Then, he kept massaging my insides, two and three fingers taking me to new heights of horny relaxation. When I was a mumbling, moaning mess, a puddle of melted bones, muscles and flesh, Victor stated that the best way to massage the prostate was with a penis. I was so gone, so relaxed and horny, I would’ve said yes to anything. So, I said _‘yes’_ …”

Cas was starting to feel angry. He couldn’t believe what Dean was telling him. How can someone abuse his best friend’s trust like that? But he had to school his features. He needed to know what else happened to Dean last night. 

-“So what happened, Dean?”

-“…I guess Victor took his clothes off, put on a condom, lubed himself up, and massaged my prostate with his penis.”

-“WHAT?” Dean was caught off guard by Cas’ anger, so Cas decided to try to control himself for Dean’s sake. “I mean, sorry Dean… How did that feel?” 

-“…Good. He’d clearly done that before… But I couldn’t help thinking that it looked like we were having gay sex. He told me we weren’t, that a gay guy wouldn’t control himself like he was and would just piston his hips wildly seeking to orgasm, but that he wasn’t, and that THAT was the difference between him having gay sex with me and him massaging my prostate with his penis.”

Cas just looked scandalized, but tried to hide it to not aggravate Dean. His friend was apparently raped last night by one of his teammates, who’d clearly taken advantage of him in his drunken state –and his naïvité about gay sex. That’s the thing about homophobia: it is a product of pure ignorance. And ignorance ALWAYS has consequences...

-“Dean, I…” Cas had to breathe deeply in order to continue. He didn’t want to be the one telling Dean that he’d had gay sex last night. But, well. Someone had to. It might as well be him. “Dean, I think you had gay sex with Victor last night.” Cas thought his friend would look more rattled by the news, but he seemed like he was taking it well.

-“…Oh. I suspected that was what was going on. But to be honest, I think I liked it. Like, _liked it_ liked it.” Cas’ eyebrows shot up to his hairline and his eyes and mouth widened at Dean’s confession. Now he was the one looking like a fish. “But…”, Dean continued. “The only thing I didn’t like was that Victor was the one who popped my gay cherry.”

Up until now, in the three and a half years Cas had known Dean, he never thought his friend would even consider being blown by a guy, let alone being fucked by one.

-“Oh, Dean…” He wanted to hug his best friend, who was looking pointedly at the floor, head downcast and crestfallen, and wouldn’t meet his eyes, as if he was afraid that Cas would judge him. He was going to show Dean that he didn’t care if he was straight, gay or bisexual. Hell, he’s been bi-curious all his life and had spent countless nights with dudes throughly ‘massaging his prostate’. “I’m sorry your first time with a man wasn’t exacty how you wanted it to be. Hopefully, your next time –if you decide to engage in gay sex in the future– will be more enjoyable and with the right person.”

-“Yeah… Wait, what? You’re not mad at me, dude? You don’t want to kick me out of the dorm for being gay and shit?” Cas wanted to look offended (as he felt a little offended; how could Dean think that?), but he couldn’t. He just laughed and threw his arm around his best friend. Then, he sighed and looked at Dean in the eyes to convey his affection and sincerity.

-“Dean, please. First of all, I don’t think you’re gay. Second, you’re acting under the belief that you’re the only one here who has had his prostate massaged with a penis.” It was Dean’s turn to look shocked now. “If we’re going to keep looking like fish, we’re going to need to rent a tank in an aquarium, not a dorm in a university housing building.”

Dean was in hysterics, laughing uncontrollably at Cas’ terrible joke. But he’d never felt more affection for his best friend, feeling like Cas truly deserved the title, and so much more. When Dean’s laughter had died, all that was left on his face was a stunning smile that Cas couldn’t look away from. Dean sighed again –this one time, in relief instead of exasperation– and looked down at the floor and then again at his friend.

-“Thanks, Cas. You’re truly an awesome roommate and friend.” After a few seconds of staring at each other, Cas decided to revert to his asshole self.

-“Now _THAT_ was gay, man!”

-“…You’re gay, man…” Cas couldn’t help but laugh at Dean’s crappy comeback of the day. “Shut up…” 

-“You know, if you’re interested in having your prostate massaged again, we could go to a place that has very good prostate masseurs.”

-“What place?” Dean asked, truly curious about the answer.

-“A gay bar.”


End file.
